


Happy Halloween

by EmilyHoyt



Category: Supernatural
Genre: F/M, Friends to Lovers, Jealous Dean Winchester, Plot What Plot/Porn Without Plot, Reader-Insert, Smut
Language: English
Status: Completed
Published: 2020-10-28
Updated: 2020-10-28
Packaged: 2021-03-09 03:48:32
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,177
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27248299
Author URL: https://archiveofourown.org/users/EmilyHoyt/pseuds/EmilyHoyt
Summary: “I hate Halloween…” Dean grumbled from his spot on the end of the couch. “I mean… I used to like it… I used to love it!” I rolled my eyes, ignoring him in an effort to be able to actually hear my movie. I’d started it about 20 minutes ago. He’d arrived within seconds to see what I was watching, then proceeded to sit there and bitch about it since!“Dean… please,” I asked. Like before, he quietened down for about 30 seconds. Then…“This isn’t even a good horror movie!” he moaned and that was it!
Relationships: Dean Winchester & You, Dean Winchester/You
Comments: 4
Kudos: 46





	Happy Halloween

**Author's Note:**

> No tricks... just lots of treats for my readers! Enjoy some Dean/Reader smut! And Happy Halloween!

“I hate Halloween…” Dean grumbled from his spot on the end of the couch. “I mean… I used to like it… I used to love it!” I rolled my eyes, ignoring him in an effort to be able to actually hear my movie. I’d started it about 20 minutes ago. He’d arrived within seconds to see what I was watching, then proceeded to sit there and bitch about it since!

“Dean… please,” I asked. Like before, he quietened down for about 30 seconds. Then…

“This isn’t even a good horror movie!” he moaned and that was it!

“Then fuck off!” I snapped, glaring at him from my end of the sofa. “I’ve been trying to watch my movie for almost half an hour and I’ve barely heard a fucking word of it!” My frustration came out in a loud huff. “I don’t talk all through your crappy movie fests! I sit down and shut up and watch with you or I leave you alone! Return the courtesy, please!”

Dean seemed to shrink in on himself for a moment and I almost felt sorry that I’d lost my temper, but he nodded his head before I could say another word.

“You’re right… I’m being a dick. Sorry, Y/N.” He offered up a little sheepish grin and I couldn’t help but return it.

“And I’m sorry for snapping.” And with that, I returned to my movie, rewinding about 10 minutes.

I had been living with the Winchesters for a while now. While I had helped on the occasional hunt, my real strength was my research abilities. I’d even managed to impress Sam with my skills, which delighted me to no end. However, my true joy was the look of shock and surprise on Dean’s face the first time I had accompanied them on a hunt. He’d been quick to tell me to stand back, but I’d charged forward and the vampire’s head rolled in front of Dean’s feet before he could finish his sentence.

When the admiration and, dare I say, hint of desire sparkled in his eyes, I knew I was in big trouble. With his gorgeous features, impressive skills and the heart of gold he hid behind his tough exterior, it was more or less guaranteed I’d fall in love with him. 

Still, it didn’t mean he didn’t piss me off sometimes. Then again, maybe that was just my sexual frustration showing through. Maybe I should go on a bar crawl tonight after all… I’d already put together a costume in case I did ⎼ a micro-mini skirt, a tight blouse, leather jacket and a set of cuffs from the dungeon made for the perfect trashy detective, especially when paired with my thigh-high leather boots! ⎼ and staying in with the grouch-cateers really didn’t appeal.

It was already late in the evening and Dean was clearly not enjoying my movie selection, so having made up my mind, I turned off the DVD player, earning Dean’s attention at that moment.

“You didn’t have to turn it off,” he said, but I was already handing off the remote to him and moving towards the door of the room.

“It’s okay. I think I’ll go out for drinks after all. It could be fun.”

“You’re going out alone?” he blurted and I couldn’t help but laugh at him.

“Yes, mother, I am… hopefully not for long...”

I don’t know what Dean did after that because I went and locked myself into my room to start getting ready. Starting with hair and make-up, I gave myself a dark smokey eye and crimson lips to go with the messy curls hanging over my shoulders. I slipped on a pale blue blouse, making sure to leave more than one button undone at the throat to show off a hint of my lacey black bra, and pulled on the tight black skirt, reminding myself not to bend over for the rest of the evening. After digging through my closet, I found my boots and pulled them on, too. I just loved how long they made my legs look. Scooping up my jacket, I made my way towards the dungeon. 

There was a cabinet full of chains and other restraints, but my goal was to arouse a man and not questions about strangely engraved cuffs. Reaching into the bottom drawer, I riffled through for a minute before finding a standard-looking set. I was just wondering where I should hang them from when a voice growled from the doorway, making me jump a foot and a half in the air.

“What the fuck are you wearing?!” Dean demanded, taking a step closer to me. Although he sounded unreasonably pissed, I couldn’t prevent the chuckle that escaped at how easily he’d scared the living daylights out of me.

“Jesus, Dean.. warn a person!” I laughed and decided the cuffs would look best hanging from one of the belt loops of the skirt. “I just needed an accessory for my outfit. And now… I’m off!” I exclaimed, moving towards the door only to be blocked by him when he took another step closer. I chuckled and tried to step around him, but he blocked me again… “Dean, enough…”

“You can’t go out like that!” he exclaimed. Now,  _ that _ made me laugh!

“The hell I can’t!” While a part of me enjoyed how protective he was of me, the other part was amused by the fact he thought he had a say in my fashion decisions. 

He crossed his arms.

“I said ‘no’...”

This was getting less amusing. I crossed mine and leaned on one hip. 

“You and what army’s gonna stop me?”

Dean’s hand was seconds away from landing on my shoulder when I caught it out of the air, stepped under his arm and twisted it behind him, secretly delighted by the look of shock on his face. He struggled for a moment before I released him with just a touch of force to move him out of my path.

“This discussion is over.” He straightened himself and his eyes burned with rage. “I’ll see you later, Dean… or maybe only tomorrow morning,” I added and turned my heel to leave, but he was faster than I anticipated. His hand closed around mine and he yanked me back inside the room.

“This discussion ain’t over yet, sweetheart,” he barked. It took me a moment to catch my balance with the slim heels on my feet. When I did, he was back in front of the doorway, preventing me from leaving. “You want to step out of here dressed like that? You have to go through me.”

“Why do you care?” I snarled. “You’re not my father, brother, boyfriend or husband. You have fuck-all right to tell me how to dress! And, even if you were, as a thirty-year-old woman, you’d STILL have no right!” The wind seemed to have been knocked out of his sails at some point, but he remained in place. “Now, let me pass… Or I will move you, Winchester.” That seemed to rekindle his anger and he straightened once more.

“You really want out that bad? Come and get it!”

I moved towards him, drawing back one fist and watched as he moved to block the assumed punch. That’s when I unclenched my hand, grabbed his outstretched wrist and swung him around until he landed against the wall, pinning his hand behind him once more. This time, though, he twisted his arm until I couldn’t hold on anymore and turned to grab at me. 

I threw myself towards the opposing wall, rolling out of the jump and coming to my feet on the other side of the room. He charged towards me and I ducked to the side, whipping my foot out to catch his calf and send him tumbling to the ground. He was about to get back up, but I managed to get on top of him first, straddling his hips and pinning his arms down by resting my whole weight on my hands.

“Enough!” I shouted, shocking him into stillness. He stared up, trying to look into my face, but my chest was in the way. “Enough of your chauvinistic bullshit! When you’re thirsty, bored, and horny, what do you do? You go to a bar, right?” I was pissed and I said a couple more things before realizing he wasn’t even listening to me anymore. “Dean!” I yelled, thoroughly pissed and about to start yelling again when he began to squirm under me. “I said stop…”

“Y/N!” he growled and yanked his hands out of my grasp to grip my hips, grinding me down onto what I was just noticing was his incredibly hard erection. I gasped and stiffened, holding my breath. His fingers spread out and his pinky brushed the skin of where my leg and hip met. This time when I gasped, it was in acute realization that my skirt was bunched around my waist right now, leaving me completely exposed in nothing more than my sheer lace thong.

“Dean⎼”

“... don’t want you going out like that,” he growled, leaning up and pressing sloppy kisses against my sternum, sucking hard. I bit my lip to hold back the whimpers as his hands migrated from my hips up to my waist, his thumb stroking the exposed skin between the rolled up skirt and the twisted up blouse. 

“Dean⎼”

“Can’t fight it anymore!” he gasped, mumbling against the skin of my chest, his scruff prickly and warm and amazing. “I need you, Y/N!” He nuzzled between my breasts and the exposed flesh tingled as his cheeks scratched them both at once. This time, I couldn’t contain my gasp. “I want you… so fucking bad!”

Yes… yes, this is exactly what I wanted… I wanted it so bad! But… no… no, we⎼

“No!” I gasped, practically jumping off of him and standing a few feet away where I felt safe enough to tug my skirt back into place. I gasped for breath, pressing my hands to my heart as it beat wildly. “No… we can’t⎼” I looked up at him and the rest of my words trailed off at the sight of him, rage radiating from his body.

“Why the fuck not?!” he snarled and, for a split second, he actually scared me. I knew he would never hurt me, but I’d never seen him so mad! “You’ll go fuck some stranger, but not me? I mean, I know I’m not good enough for you! That’s a given! But seriously?!”

My mind short circuited for a couple of seconds and I stared up at him, listening and yet not hearing all at once. It took a good ten seconds before the words made it through the haze of my brain and, at that point, Dean had started to make his way to the door. Luckily, I was closer, so I swung it shut and leaned against it, stopping him in his tracks. I stared at him and a ghost of a smile flickered over my lips.

“This discussion ain’t over yet, sweetheart,” I murmured, my chest still heaving with each breath. I took a single step closer to him. When he didn’t flinch, I took another. Then, several more until I was standing right in front of him. The tip of my tongue swiped over my dry lips for a split second before I placed my hands on his chest. I tilted my head up to look into his eyes. 

“Why don’t you want me dressing like this?” I asked softly, watching him swallow hard.

“ ‘Cause it’ll attract other guys…” he admitted in a breath. The corner of my mouth quirked for just a second.

“So… why does that matter?”

“ ‘Cause I want you all to myself.” His honesty was so direct that it nearly took my breath away. A smile curved my lips and my teeth caught my lower lip for a second before his hands cupped my face, his thumb pulling it loose.

“You all mine in return?” The air left him in a whoosh and he smiled, for the first time in a long time, the kind that made his green eyes spark with joy.

“Always.”

In a blink, his hand moved to tangle in my hair and he crushed his lips to mine, sucking and nibbling and driving me so out of my mind that it took a couple seconds before I could even respond. Once I did, though, my hands curled around his neck, my nails scratching the base of his scalp, and I hummed in delight at the growl that came from his throat.

“Fuck!” he groaned as I pressed myself against him, the bulge of his jeans against my lower abdomen. His head fell back and I took advantage to kiss and tease his exposed throat, latching my lips onto one spot that made him grunt and sucking until it began to turn a gorgeous shade of purple.

“Y/N!” he moaned and one hand left my hair to grab as much of my ass as he could, grinding me against him, making us both gasp. Holding my tight against him, he turned me around and walked me backwards until my ass met the wooden table in the middle of the dungeon. His hands went to my hips and hiked me up onto the edge, letting me skootch back a couple of inches while his fingers went to work undoing my blouse.

“Dean…” I breathed out between kisses, my own fingers attacking the belt of his jeans, fighting the leather strap through the buckle before reaching for the button on the denim. Just as I was about to slip the metal through the hole, he slapped my hands away and got to his knees, inching my already-too-short skirt up what little of my things it covered. “Dean, please…”

“I’ve been dreamin’ about tastin’ this pussy since as long as I can remember!” he mumbled, kissing his way up my thigh while his fingers moved my thong aside and swiped up my slit. I sucked in a breath at the first touch against my clit, holding it, waiting for the next contact. His hands moved back to curl around my ass to drag me closer to the edge - closer to him. Then, they slid along my thighs to my knees to spread my legs wide from him. Hooking his index around the already soaked fabric, he yanked hard and the thin straps snapped, allowing him to toss it aside. I was about to scold him for ruining part of a matching set when his mouth finally made contact with my wet heat.

“Oh, fuck!” His lips and tongue were even more talented than I’d fantasized, licking into me, sucking on my clit, his teeth scraping across the bud, taking my breath away. All I could do was choke and moan my pleasure, barely able to catch my breath under his ministrations. “Yes!” He pressed his face right into my bare crotch and shook his head back and forth, sucking harder on me. Then, he eased off and tongued more gently around my lips, occasionally catching them lightly between his teeth. “Oh, fuck, yes!” When he released my labia from his little nibbles, he soothed them, swiping his tongue over them, pressing sloppy kisses against me. 

Then, he released my knees and flattened his hands right at the joint of my hips and spread me as wide as he could, his thumbs catching my mons just enough to part them. I held my breath, waiting to see what he was about to do. When his tongue thrust into me, long and stiff, I let out a short scream that dissolved into whimpers and moans as he fucked me with his tongue, sometimes pausing inside to run the tip all around my walls.

“Fuck, Dean!” His tongue was so deep inside me that his mouth managed to close over my labia and he sucked on my lips while tonguing me into oblivion. I was wriggling something awful on the table and, for the briefest of seconds, I managed to ponder if it was solid enough to hold my squirming body, but Dean’s mouth wiped all other thoughts from my head when he stopped for a second. I hoped he was about to stand up and shove his rock hard cock into me. Instead, one hand left my spread hips and I felt the tips of two fingers nudge at my entrance.

“Oh…” They wormed gently into me and he began to thrust them ever so leisurely. I whimpered and my body convulsed and curled in on itself at the torturously slow pace he’d set, taking several full seconds to withdraw his fingers completely before taking just as long to ease them back in. When he maintained the pace while curling his fingers just enough to stroke that rough spot of my vagina, I felt tears prickle at the corner of my eyes.

“Dean, please!” I begged, almost crying with desperation. My whole body was teetering on the edge and his deliberately unhurried pace was just enough to keep me at the edge without actually pushing me over. I was so close. He stopped his in and out movements for a moment, letting just his fingertips move inside of me, massaging firm and slow against my G-spot. 

“Please!” I cried out, but he withdrew, leaving me hanging for a moment. I stared down at him between my spread legs. “You’re mean,” I groaned, but the sight of his cheeks and chin coated in my slick almost sent me back to the edge without him even touching me.

“I’m not mean; I’m patient,” he said lowly, his voice raw with desire. Then, with my eyes on his, he pressed his hand back between my thighs, but this time, he’d added another finger. When he first pushed into me, my body collapsed back onto the table with a thud, the stretch of my pussy making my eyes roll into my head. He started back in with that same agonizing pace and my orgasm came rushing back to the edge, hovering there once more at his slow movements.

“Please, Dean! Please!” I cried out. My second ‘please’ still hung in the air when I felt him shift his weight and, without warning, he curled his fingers, began sawing them in and out of me at a wild pace and closed his lips around my aching clit. The scream was torn from my throat as my whole body jolted with pleasure, my orgasm cresting within seconds. My head twisted from side to side as he continued to tongue and suck at the bundle of nerves, his fingers rubbing with determination against my G-spot. 

I could barely catch my breath when he began trembling his arm and the reverberations echoed down through his hand to his fingertips inside me. A second wave a pressure exploded through my body, everything seizing while a stream of my juices spilt out of me. Dean growled at the sight and his mouth began to devour my whole pussy, licking and sucking everywhere, trying to gather up every little drop he could. Some trickled down my folds along the crack of my ass, but that didn’t stop him. His tongue teased at the pucker between my cheeks, making me tremble on the table, until he was satisfied that nothing had escaped him.

“Fuck, that was hot!” he gasped, getting to his feet and lowering his jeans in one fluid move, taking his boxers with them. I was laying there, panting and exhausted, but the sight of him had me pulling on my reserves of energy to try and sit up, reaching out to touch him. “No!” he grunted, surprising me into stillness. “I’m too close… You can have your fun later.” He palmed my folds, gathering slick and using it to prep himself. “Right now… I need you. Need this,” he grunted as he pressed his tip to my opening. In that moment, I was grateful for his earlier actions; his girth was deliciously wide and his three fingers would make taking him in much easier.

“Do it!” I gasped, wriggling against him, listening as his breath hitched in his throat. Still, he didn’t move for another several seconds and, just as I pushed up onto my elbows to ask what he was waiting for, he slid in in one fluid movement, forcing a little scream of pain, pleasure and surprise from me. 

“Yes!” I was still so tight from my two orgasms and he was so big inside me, filling me up like no one ever had before. He dragged ever so slowly out of me and I thought for a moment that he was starting that shit again, but he slammed his hips into mine, forcing another shout out of me.

“So tight! So warm and wet for me!”

I’m not sure if his words were directed at me or if he was talking to himself, but I felt my orgasm creeping near once more. Just the sensation of having him inside me… after so long… I whimpered as he set his pace, firm and pointed, just this side of frenzied, and it felt amazing. I felt his hands slide up and down my thighs for several passes before they hooked under my knees and lifted until he could drape them over his shoulders. On his next thrust, I was seeing stars, the new angle driving him into my G-spot, then on deeper than before.

“Fuck!” I wondered why my voice suddenly had an echo, but when Dean’s eyes locked with mine, I realized we’d both spoken at the same time. A smile quirked my lips for a moment before he leaned over me, folding me even further in half. The muscles in my thighs protested, but it felt too damn good for me to give any kind of damn! My hands slammed down on the table, latching onto the edge, holding on as he hammered into me, his speed increasing as his resolve decreased.

“So fuckin’ close, baby,” he groaned into my ear, curling down to kiss my throat for a moment before lifting himself up to stare into my eyes. “You got one more in you, sweetheart?”

Aside from whimpers and grunts every time he thrust up into me, I was beyond words, so I just nodded quickly, my breath catching in my throat when one of his hands skimmed over my breasts, which I only now realized were bare, Dean having tucked the lace fabric under on each side. My head tucked back at the feel of his calloused fingers swiping and squeezing at my hardened nipples. He grunted when a particularly tight pinch caused me to clamp down on him.

“Come for me, Y/N!” he groaned and his hand left my breast to squeeze down between us, finding my clit with his thumb. I jolted as I felt myself being pulled under. “Come for me! Come  _ with _ me!”

“DEAN!” His name flew from my throat as white-hot pleasure pulsed through my body. My walls bore down on him and he managed to thrust once more through my tightness before he came with a scream of my name and I felt his cum coat inside of me, pushing me even higher. I could feel my juices trickling around his pulsing cock, dripping down my ass and his thighs while we stayed locked like that, both our bodies rigid as the waves rolled through us.

Eventually, our bodies gave out and Dean slumped over me while I tried, as gracefully as possible, to lower my legs from his shoulders. He caught them at the last second, breaking their fall and placing them a bit more gently onto the table. His torso was draped over mine, bent at the waist, his ass in the air, while I gently ran my fingers through his damp spiky hair, taking deep pulls of air into my chest. 

“I’ve been… wanting to do that… so long.” His words were punctuated with deep pulls of air and gentle kisses against my shoulders. He leaned up and ran a finger along the side of my cheek.

“You tryin’ to say you like me, Winchester?” I teased, nibbling my lower lip, smiling up at him. His expression sobered a little and it felt like he was staring right into me.

“I’m tryin’ to say ‘I love you’...”

The smile spread across my cheeks and I could feel them heating.

“Really?” I squeaked, happiness surging through me. Suddenly, he seemed like he was withdrawing from me. “Hey!”

“It’s alright if… I mean, you don’t have to…”

“Jesus, Winchester! Of course, I love you, too!” A little chuckle escaped at the obvious relief in his expression. “Dumbass!” His eyes narrowed with mock anger, but the grin stayed plastered on his face. “So… still hate Halloween?” His eyes went wide as he stared down at me.

“Are you kidding? I love Halloween!”

**Author's Note:**

> Thanks! Please drop a review! I live for them!


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